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Why did Yaakov send messengers to Eisav in Seir when his original plan was to go directly to Yitzchok in Canaan? The shiur examines the textual evidence that Yaakov changed his itinerary, explores why malachim of Eretz Yisrael could travel to Edom (either because it's part of the ten lands or following the Kuzari's principle), and probes what event—possibly the confrontation with Lavan—prompted this strategic shift.
Rabbi Zweig opens with a close reading of the opening pasuk of Parshas Vayishlach: "Vayishlach Yaakov malachim lefanov el Eisav achiv artza Seir sadeh Edom." The word "lefanov" (before him) indicates Yaakov is sending messengers ahead of himself to where he is going. Yet the previous parsha clearly states Yaakov left Padan Aram "lavo el Yitzchok aviv artza Canaan"—his destination was Canaan, to his father Yitzchok in Hebron. Why then does the pasuk indicate he's heading to Eisav in Seir, which is in Edom, a completely different country? The difficulty deepens when we examine Bereishis 36:6, which shows that Eisav did not relocate to Seir permanently until after Yaakov had already arrived in Eretz Yisrael. Eisav was essentially a "snowbird" in Seir—he had holdings there but his primary residence and family were in Eretz Canaan. The shiur determines this meeting occurred at the end of winter based on the subsequent mention of Sukkos (סוכות), where Rashi (רש"י) indicates summer and winter periods. If Eisav lived in Canaan and would be returning there, why couldn't Yaakov simply wait to encounter him in their father's land? What necessitated this urgent detour?
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Why does the Midrash connect Pharaoh's expulsion of the Jews to the mitzvah of shiluach hakan? The shiur develops a chiddush that Pharaoh's sin wasn't only drowning the children, but the insensitivity of expelling the parents afterward. The deeper analysis reveals that Pharaoh may have valued the Jews greatly and wanted to control them—making his expulsion an act of tremendous cruelty, not liberation.
Why does Moshe respond to the splitting of the sea with shirah rather than praise or thanksgiving? Rashi's use of "al libo" reveals that shirah is an emotional expression—a response of love to love. When Hashem shows personal care, the only adequate response is "I love You too," not mere gratitude or praise, and this principle applies to all relationships.
Bereishis 32:4-5, 33:17-18, 36:6
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